Hydrochloric Acid → HCID 10781398, compound

HRID 2418589Notes

Reaction equation

HRID 2418589 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:9]([NH:11][C@H:12]([C:20]([O:22][CH3:23])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>C(OCC)(=O)C>[NH2:1][C@@H:2]([C:9]([NH:11][C@H:12]([C:20]([O:22][CH3:23])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10645358HCID 10645358, compound

Product 1

HCID 10781398HCID 10781398, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Condensation of BocDPhgOH (5.0 g.) and HPheOMe hydrochloride salt (4.3 g.) by the mixed anhydride method using isobutyl chloroformate gave BocDPhg-PheOMe in 98% yield. De-t-butoxycarbonylation of BocDPhg-PheOMe (4.23 g.) using hydrogen chloride in ethyl acetate gave HDPhg-PheOMe in 100% yield. Condensation of BocProOPFP (3.81 g.) and HDPhg-PheOMe hydrochloride salt (3.5 g.) by the activated ester method gave BocPro-DPhg-PheOMe in 74% yield. Hydrazinolysis of Bocpro-DPhg-PheOMe (3.57 g.) gave BocPro-DPhg-PheNHNH2 in 80% yield.

Sources & evidence

ORD record
ord-16859f53302d42508c381ce0c696befe
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

Loading…